Acetic Acid → HCID 66661251, compound

HRID 1664721Notes

Reaction equation

HRID 1664721 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2]1.C(O)(=O)C.C(O[C:26]1(O[Si](C)(C)C)[CH2:28][CH2:27]1)C.[BH3-]C#N.[Na+].C1COCC1>CO>[CH:26]1([N:9]2[CH2:10][CH2:11][C:6]3([CH2:1][CH2:2][N:3]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4][CH2:5]3)[CH2:7][CH2:8]2)[CH2:28][CH2:27]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 15296367tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 66661251HCID 66661251, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (250 mg, 0.98 mmol) were dissolved in 10 ml of absolute methanol. 3 g of molecular sieves (3 Å, which had been dried beforehand under high vacuum) were added to this solution. Under argon, glacial acetic acid (0.55 ml, 10 eq.), [(1-ethoxycyclopropyl)oxy]trimethylsilane (0.69 ml, 3.5 eq.) and 4.4 ml of a 1 M NaCNBH3 solution in THF (4.4 mmol, 4.5 eq.) were then added successively. After stirring at RT for 20 minutes, the mixture was heated to 60° C. and stirred at this temperature for about 15 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was taken up in dichloromethane, washed successively with 1 M NaOH solution and NaCl solution, and dried over MgSO4. After the solvent had been removed under reduced pressure, the product was obtained as a colorless oil.

Workup

  1. custom3 g of molecular sieves (3 Å, which had been dried beforehand under high vacuum)
  2. additionwere added to this solution
  3. temperaturethe mixture was heated to 60° C.
  4. stirringstirred at this temperature for about 15 h
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washwashed successively with 1 M NaOH solution and NaCl solution
  8. dry with materialdried over MgSO4
  9. customAfter the solvent had been removed under reduced pressure
  10. customthe product was obtained as a colorless oil

Sources & evidence

ORD record
ord-242bcb28caed4e6b87258778b6b04238
Source dataset
uspto-grants-2011_10
Patent number
US08039480B2

Reaction notes

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